Triethylamine → N-(6-bromoquinolin-2-yl)cyclohexanecarboxamide

HRID 879643Notes

Reaction equation

HRID 879643 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[N:3]=1.CCN(CC)CC.[CH:20]1([C:26](Cl)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Br:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:1][C:26]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:27])[CH:11]=[CH:10]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 111836666-Bromoquinolin-2-amine

Product 1

HCID 86700452N-(6-bromoquinolin-2-yl)cyclohexanecarboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-6-bromoquinoline (250 mg, 1.121 mmol) in CH2Cl2 (7 mL) was added Et3N (0.94 mL, 6.726 mmol) and DMAP (137 mg, 1.121 mmol) followed by cyclohexanecarbonyl chloride (0.46 mL, 3.362 mmol). The reaction mixture was stirred at rt for 20 min and then diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 40% ethyl acetate/hexanes) to give the product. LCMS-ESI+: calc'd for C16H18BrN2O: 333.0 (M+H+); found: 333.1 (M+H+).

Workup

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (silica gel, 0 to 40% ethyl acetate/hexanes)
  6. customto give the product

Sources & evidence

ORD record
ord-1e7006e14e864e8f97188586454dc1cd
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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